Winona Grant embarks on a summer-long visit to NYC to house-sit for her great-aunt after a nasty break-up with her boyfriend Paul. But when her aunt commissions neighbor Steve Monti to tour Winona around, they strike a deal. Winona has too many deadlines to play tourist, and Steve is looking for a distraction from his looming gallery opening. So Steve goes on the tours by himself, and Winona reports back to her aunt as if she'd gone too. The longer this happens, the more Winona wants to change her mind. Seeing the city with Steve might be the perfect solution to forgetting about Paul.